Resinous material and process of making



' Patented Sept. 18, 1945' 2,384,840 assmoos MATERIAL AND PROCESS or MAKING Charles G. Moore, River Forest, Ill., asslgnor to The Glidden Company, Cleveland, Ohio, a corporation of Ohio No Drawing. Application November 8, 1041, Serial No. 418,383

3 Claims.

This invention relates to a process and a resulting product which may be described as either a synthetic oil or a synthetic resin. The product is of the nature of synthetic resins but it is primarily used as an oil, and is a viscous liquid in physical appearance. This product, described below, may be used in conjunction with other oils, and/or resins to produce varnishes, inks, and for coating and impregnating purposes, either clear or pigmented. a

It has long been recognized that when maleic anhydride is reacted with a monoglyceride or a drying or semi-drying oil, the acid number of the resulting product cannot be reduced below 80-100. Furthermore, the product of such a reaction is very heavy in body and is seldom miscible with other drying and/or semi-drying oils. Such a product is also insoluble in petroleum solvents. If it is attempted to reduce the acid number below this point, the material gels, becomes insoluble in solvents such as ketones, esters and others as well as petroleum solvents, and finally chars. The explanation for this action is that polymerization takes place more rapidly than esteriflcation with the result that an insoluble gel is produced before the acid number is suillciently lowered. These statements hold foramounts of material or 2000 grams and upwards. If smaller amounts of reacting substances, such as 200 grains are reacted together, the acid number may be reduced below 80 and yield a product which is soluble in ketones, esters and petroleum solvents, as well as miscible in all proportions with other drying and semi-drying oils.

Rosenblum, in United States Patent No. 2,063,-

855 has disclosed a method of overcoming this dimculty by preparing a different product. In his patent, he prepares a di-glyceride of low acid value and combines this product with maleic acid or anhydride to produce a product of low acid value. He recognizes in his. patent that the monoglyceride when reacted with suflicientmaleic anhydride to combine with the remaining free hydroxyls, gives a product of high acid value (80-100) as described in the previous paragraph. Rosenblums product may be described as a polymer of the following product, together with free or semi-combined acid:

Hie-000R n -ooca md-ooc-cn rnc-ooc- H Hi l-000R Hid-000s where It represents the radical of a fatty acid obtained by the hydrolysis of a drying or semidrying oil.

The product described in this invention may be represented as consisting primarily of polymers of the following compound, together with a limited amount of free or semi-eomlnned acid;

rn-o-ooos 11- -ooo-cn v in which "R." represents the radical of a fatty soluble in solvents such as esters, ketones, petroleum and coal tar hydrocarbons. It is also misciblo in all proportions with other drying and semi-drying oils. It may also be cooked together with various resins and oils, and when so cooked.

the acid value may be still further reduced. The product obtained by this cooking process may be made into a varnish by dissolving in suitable solvents and adding drie'rs to the product.

In a preferred form of this invention one mol. of glycerine is heated together with one moi of soya oil fatty acids until the acid value is reduced to about 2. This monoglyceride is then reacted at 2'50-300 F. with one moi of maleic anhydrida until the acid value is reduced to about 30-60, or below 80. The resulting product is miscible with oils such as linseed oil, fish oil, soya bean oil,

sunflower oil, China-wood oil, etc. It is important that the monoglyceride and maleic anhydride be heated at a low temperature so that the rate of esterification of the monoglyceride and maleic anhydride will proceed at a more rapid rate than the polymerization of the reaction product. If the mcnoglyceride and maleic anhydride are heated together at a higher temperature, 450 F., for example, the polymerization proceeds at a much more rapid rate than the esteriflcation and results in the material formin an insoluble gel on cooling down before the acid value can be reduced below -100, the only exception being, if-very small amounts (200-300 gins.) of the material are reacted togetherv and cooled down quickly.

The fatty acids and glycerine are heated together at 450 F., until a low acid value is obtained, the monoglycer-ide so formed is then cooled to 300 F.,

and the meleic enhydride is added. The whole-is then heated at 25l-300 R, until the acid value is reduced to 30-50.

Example 2 Grems Linseed fatty acid monoglyceride 1610 Meleic anhydride 432 eseeeee Having described the invention what is claimed l. The process which consists in reacting glycerine and fatty acids selected from the class consisting of drying and semi-dryin ail fatty acids in substantially equimolecular proportions until e substantially neutral product is formed, and heating the resulting reaction product with substantially an equimolecular quantity of maleic enhydride at a. temperature of 250-300 F. for a. time suficient to reduce the acid number to about 60-30.

2. A resinous product resulting from the process of claim 1. v

3. A resinous product resulting from the process of claim 1 dissolved in a, glyceride oil selected from the class consisting of drying and semi drying glyceride oils.

' CHARLES G. MOORE. 

